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How to get fromWindsor to Pittsfieldby plane, bus, train (Amtrak), bus (Greyhound), car, or train

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There are 7 ways to get from Windsor to Pittsfield by plane, bus, train (Amtrak), bus (Greyhound), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Albany County Airport, bus

    best
    1. Fly from Detroit (DTW) to Albany County Airport (ALB)plane plane DTW - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    6h 36m
    $111–617

  2. Fly to Bradley International Airport, train

    cheapest
    1. Fly from Detroit (DTW) to Bradley International Airport (BDL)plane plane DTW - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    7h 51m
    $94–460

  3. Train

    1. Take the train from Windsor to Aldershottrain train
    2. Take the train from Aldershot to Albanytrain train
    3. Take the train from Albany-Rensselaer Amtrak Station to Pittsfield Amtrak Stationtrain train
    15h 38m
    $167–492

  4. Bus (Greyhound)

    1. Take the bus from Detroit Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Albany Bus Terminal, NYbus bus
    3. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    16h 20m
    $105–207

  5. Drive 569.9 mi

    1. Drive from Windsor to Pittsfieldcar car 569.9 mi
    10h 18m
    $131–189

  6. Fly to Laguardia Airport, train

    1. Fly from Detroit (DTW) to Laguardia Airport (LGA)plane plane DTW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    9h 19m
    $175–508

  7. Fly to Boston Logan Airport, train

    1. Fly from Detroit (DTW) to Boston Logan Airport (BOS)plane plane DTW - BOS
    2. Take the train from Boston to Pittsfield Amtrak Stationtrain train
    9h 5m
    $556–1,411

Windsor to Pittsfield by train

Calendar7Weekly Trains
Duration15h 38mAverage Duration
Ticket$167Cheapest Price
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Questions & Answers

Map of how to get from Windsor to Pittsfield.ExpandLaunch map view
  • Distance: 557 mi
  • Duration: 6h 36m

What companies run services between Windsor, ON, Canada and Pittsfield, MA, USA?

You can take a train from Windsor to Pittsfield Amtrak Station via Aldershot, Albany, and Albany-Rensselaer Amtrak Station in around 15h 38m. Alternatively, you can take a bus from Detroit Bus Station to Pittsfield via Cleveland Bus Station and Albany Bus Terminal, NY in around 16h 20m.

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